60372
Secoisolariciresinol
≥95.0% (HPLC)
Synonym(s):
(2R,3R)-2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol
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About This Item
Empirical Formula (Hill Notation):
C20H26O6
Molecular Weight:
362.42
Beilstein:
6611290
EC Number:
MDL number:
UNSPSC Code:
41116105
PubChem Substance ID:
NACRES:
NA.21
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Assay
≥95.0% (HPLC)
form
solid
SMILES string
OC[C@@H]([C@H](CO)CC1=CC=C(O)C(OC)=C1)CC2=CC(OC)=C(O)C=C2
InChI
1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
InChI key
PUETUDUXMCLALY-HOTGVXAUSA-N
Application
Secoisolariciresinol is a metabolite of secoisolariciresinol diglucoside (SDG), an antioxidant present in flaxseed.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Physical form
mixture of enantiomers of the (R*,R*)-diastereoisomer
Other Notes
Component of functional food. Flaxseed lignan with antioxidant activity
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Hisashi Nishiwaki et al.
Bioscience, biotechnology, and biochemistry, 75(9), 1735-1739 (2011-09-08)
The larvicidal activity against Culex pipiens of all stereoisomers of dihydroguaiaretic acid (DGA) and secoisolariciresinol was measured, and these DGAs were found to be potent. Sixteen (-)-DGA derivatives were then newly synthesized to analyze their structure-activity relationship. Two derivatives monohydroxylated
Shiori Tominaga et al.
Food & function, 3(1), 76-82 (2011-10-28)
Flaxseed lignan, secoisolariciresinol has been reported to possess health benefits. We previously synthesized each stereoisomer of secoisolariciresinol and found that (-)-secoisolariciresinol reduces lipid accumulation and induces adiponectin production in 3T3-L1 adipocytes. Here we show the effects of (-)-secoisolariciresinol on high-fat
D D Kitts et al.
Molecular and cellular biochemistry, 202(1-2), 91-100 (2000-03-08)
The antioxidant activities of the flaxseed lignan secoisolariciresinol diglycoside (SDG) and its mammalian lignan metabolites, enterodiol (ED) and enterolactone (EL), were evaluated in both lipid and aqueous in vitro model systems. All three lignans significantly (p < or = 0.05)
Carol J Fabian et al.
Cancer prevention research (Philadelphia, Pa.), 3(10), 1342-1350 (2010-08-21)
Preclinical and correlative studies suggest reduced breast cancer with higher lignan intake or blood levels. We conducted a pilot study of modulation of risk biomarkers for breast cancer in premenopausal women after administration of the plant lignan secoisolariciresinol given as
M R O'Neil et al.
Domestic animal endocrinology, 37(3), 148-158 (2009-06-30)
To evaluate the estrogenic potential of secoisolariciresinol diglycoside (SDG) found in linseed meal (LSM) on visceral organ mass, IGF-I, and thyroid hormone (T(3) and T(4)) concentrations, 48 multiparous, ovariectomized ewes (54.6 +/- 1.1 kg) were used in a 3 x
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